Round: 26 Ground: Clay
| ITF Japan F7 Qual | 2016/06/05 01:00 | Yusuke Takahashi v Kaito Uesugi | 6-4,6-0 |
| ITF Japan F8 | 2016/06/15 06:25 | Issei Okamura v Yusuke Takahashi | 3-6,0-6 |
| ITF Japan F7 | 2016/06/11 03:40 | Yusuke Takahashi v Sho Katayama | 2-6,0-6 |
| ITF Japan F7 | 2016/06/10 01:00 | Yusuke Takahashi v Chan-Yeong Oh | 6-1,6-0 |
| ITF Japan F7 | 2016/06/08 03:00 | Yusuke Takahashi v Ryota Kishi | 6-3,6-2 |
| ITF Japan F7 | 2016/06/06 03:00 | Yuya Kibi v Yusuke Takahashi | 1-6,3-6 |
| ITF Japan F7 Qual | 2016/06/05 01:00 | Yusuke Takahashi v Kaito Uesugi | 6-4,6-0 |
| ITF Japan F6 | 2016/06/02 02:50 | Duckhee Lee v Yusuke Takahashi | 6-3,6-0 |
| ITF Japan F6 | 2016/05/31 05:25 | Yusuke Takahashi v Keisuke Watanuki | 6-3,6-4 |
| ITF Japan F8 | 2016/06/15 05:50 | Kaito Uesugi v Kousuke Ogura | 6-1,6-3 |
| ITF Japan F8 | 2016/06/13 01:00 | Koichi Sano v Kaito Uesugi | 2-6,4-6 |
| ITF Japan F8 | 2016/06/12 01:00 | Kaito Uesugi v Taiki Hashimoto | 7-5,6-2 |
| ITF Japan F8 | 2016/06/11 04:00 | Kaito Uesugi v Tomohiro Masabayashi | 6-1,6-2 |
| ITF Japan F7 Qual | 2016/06/05 01:00 | Yusuke Takahashi v Kaito Uesugi | 6-4,6-0 |
| ITF Japan F6 | 2016/05/31 05:10 | Andrew Whittington v Kaito Uesugi | 3-6,6-4,6-4 |
| ITF Japan F5 | 2016/04/05 07:30 | Arata Onozawa v Kaito Uesugi | 6-3,6-4 |
| ITF Japan F4 | 2016/03/29 01:00 | Rigele Te v Kaito Uesugi | 3-6,6-1,6-3 |